4-Aminobenzonitrile → HCID 58636767, compound

HRID 1158994Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][O:7][C:8]1[C:16]([CH3:17])=[N:15][C:14]([CH:18]2[CH2:20][CH2:19]2)=[CH:13][C:9]=1[C:10](O)=[O:11])#[N:2].[NH2:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1>>[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][O:7][C:8]1[C:16]([CH3:17])=[N:15][C:14]([CH:18]2[CH2:19][CH2:20]2)=[CH:13][C:9]=1[C:10]([NH:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1)=[O:11])#[N:2]

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 58636735HCID 58636735, compound

Product 1

HCID 58636767HCID 58636767, compoundYield 61%

Procedure

The amide coupling of 3-(3-cyano-benzyloxy)-6-cyclopropyl-2-methyl-isonicotinic acid (189) (112 mg, 0.4 mmol) and 4-amino-benzonitrile (51 mg, 0.4 mmol), as described in Example 67, gave 3-(3-cyano-benzyloxy)-N-(4-cyano-phenyl)-6-cyclopropyl-2-methyl-isonicotinamide (190) (90.0 mg, 61% yield).

Sources & evidence

ORD record: ord-6941cdd31a634b07973afb4d739b7764
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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